


In Which Dean Is Oblivious and Cas Finally Says It Straight To His Face

by REVVIII



Category: Supernatural
Genre: Crack, Everyone Is Alive, Fluff, Fluff and Crack, Humor, M/M, Meddling, Mild Language, Shipping, mature for later chapters, messed up timeline, they all live together
Language: English
Status: Completed
Published: 2017-05-11
Updated: 2017-06-18
Packaged: 2018-10-30 13:59:34
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 16,126
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10878246
Author URL: https://archiveofourown.org/users/REVVIII/pseuds/REVVIII
Summary: Charlie, Jess, and Jo are masters of meddling. They already got Sam and Gabriel together in the span of a week - so now it's time for Destiel.





	1. Sam Is Just Tired of Their Eye-Fucking. Honest.

 

 

One month ago, Sam had found himself pressed against the wall by a very unexpectedly _nippy_ archangel smothering his body with his own, completely oblivious to the ridiculous number of photos a very triumphant Charlie was taking of them with her iPhone from behind the crack in the door, before a gleeful Jess and Jo pulled her away from the room to give Sam and Gabriel some privacy.

And now, Charlie, Jess, and Jo sat next to each other on Charlie’s bed across from Sam, who looked quite apprehensive as he perched precariously on Charlie’s now very small-looking chair. The girls had a feverish glint in their eyes, which, based on past experience, could either be something very good or very bad.

“Um, guys, what am I here for again?”

Charlie had the widest grin that Sam had ever seen on her face. “Dean and Cas are out for another few hours, so this is the _perfect_ time to talk about this.” She leaned forward, looking like a very, _very_ mischievous pixie, pressed her index finger to her thumb on both hands, and brought the unified fingers together while making a kissing noise.

“Uh…what’s that supposed to mean?”

Charlie leaned forward even more. “We are going to get Dean and Cas together,” she whispered excitedly.

Sam raised his eyebrows. “Um, great. And…what does that have to do with me?”

Charlie gave him a look.

“I mean, of course I want them to get together, don’t you think I’m tired of all the eye-fucking that’s been going on? But why do I have to be a part of it? I think you guys have got it all handled, right?”

“True, we got you and Gabe together, didn’t we? And you guys have gotten it on pretty well, if the banging against the wall every Tuesday night is anything to go by,” Jo mused, and Sam gave her his best bitchface, which she promptly ignored.

Jess let out a dramatic sigh. “But honestly, you Winchesters have got to be the most emotionally _dense_ couple of people I have ever met. It took us _forever_ to get you and Gabe to realize exactly how infatuated with each other you were, and we could really use your help this round, since your brother is even _more_ emotionally dense than you are.”

“Exactly,” Charlie agreed. “You know Cas and Dean better than any of us, and since they’re _so_ emotionally dense, we need you to help us figure out the best way to get the message across to each of them.”

Sam squirmed. “I’m really not great with all this…meddling stuff, you know?”

“Sam, pleeease? We really need you.” Jess looked at Sam with her best puppy eyes. They’d been best friends since childhood. Her puppy eyes had worked on him when he was four, and she’d be damned if they didn’t work on him now.

Sam sighed and rubbed his face with his hands, already caving as Jess knew he would. “Okay, okay. Well, if anything, it’s Dean you’re gonna have to work on. Cas has been giving him hints for _years_ , but Dean hasn’t picked up on them. It’s like he’s blind.”

“Hm. Okay, well, first we’ll need a lot more information about those hints, since we’ve only been here for the past month and a half and I’m sure we missed a lot,” Charlie decided. Clearly, she was the leading brain in this project. “Sam, what can you tell us about what Cas has been doing that’s oh-so-obvious to literally everyone except Dean?”

Sam sighed again. “You mean aside from staring at him the entire time he’s within eyeshot, standing about six inches away from him at any opportunity he’s got, getting ready to smite everyone with deadly angel of the Lord rage whenever Dean’s in any kind of danger?”

Charlie rolled her eyes. “Yes, apart from that.”

Sam sighed yet again. “Okay. Well, first, we had a pretty bad hunt a few months ago. Well, it wasn’t _too_ bad, we managed to get them all, but Dean got pretty scratched up in the process. Cas was all over him when we got back, practically carrying him to his bed, watching over him when he was sleeping…you know, basically being a mother hen. Meanwhile _I_ was over there tending to my _multiple stab wounds_ all by myself since Cas would rather watch Dean snore than spare a second to help me out with his angel mojo.”

Charlie crossed her legs and rested her elbows on her knees, leaning forward eagerly. “Wait, did you say watching over him when he was sleeping? The whole time?”

Sam looked miffed at her lack of sympathy towards his pitiful situation but decided not to pursue it. “I mean…yeah, pretty much. You should’ve seen the look on his face too. Such a sap.” Sam shook his head. “Dean doesn’t get it though, that Cas literally does this just for him.”

“Hm.”

“And then New Year’s Eve, we were watching the news in Times Square, the crystal ball drop, whatever. Well, Dean and Cas were, I was kind of off in the kitchen behind them reading. They were sitting on the couch and the camera went around showing all the New Year’s kisses, and Cas said that he wanted one.”

“ _What_?!” all three girls exclaimed in unison.

Sam winced. “I mean, he sort of just mumbled it, but either way Dean still didn’t get it.”

Charlie groaned.

“To be fair,” Jess interjected thoughtfully, “It doesn’t seem like Cas has made it clear that he only does this stuff for Dean, or that it’s directed at Dean. For all Dean knows, this is just who Cas is as a guy.”

Charlie looked at her thoughtfully. “Good point. We could start there? Just tell Cas to make the hints more direct and see how that works out?”

Alarm flashed across Sam’s face. “Whoa guys, wait, is Cas in on this?”

Jo shook her head. “Not yet, he isn’t.”

“What do you mean, ‘not yet?’”

“Gabe has always been pretty open and direct, as far as we could tell,” Jess explained. “And you’re _much_ less emotionally stuck-up than your big bro. Meddling with you two without you really knowing about it –”

“Oh, I knew about it,” Sam muttered.

“Okay, you knew about it. But you weren’t really playing an active role in it, and it worked, because you and your archangel are pretty open and just needed a little push in the right direction. Plus, you two already kinda knew that you had the hots for each other. Cas and Dean just…aren’t the same. We have to have at least one of them in on it, and our bet’s on Cas.”

Sam frowned and sat back. “I think you’ll scare him off if you just spring it on him like this. He’ll use his angel mojo and just…disappear somewhere and you’ll never see him again.”

Charlie pursed her lips. “Fair point. He does seem pretty skittish sometimes. We’ll meddle first, get a feel for things, and then we’ll gradually bring him in on it if it doesn’t seem like our meddling is working. Any ideas, anyone?”

“What about getting them alone in the same room? Like, completely alone, both awake, no Sam lurking in the background,” Jo suggested.

“No, that wouldn’t work.” Sam shook his head. “You know how many times I’ve tried that? What do you–”

“Wait, what?” Jo looked incredulous. “So you’ve _already_ meddled? Oh my God!”

Sam looked embarrassed and ran a hand through his hair. “Look, it’s not like I _want_ to hear my brother fucking an angel – oh God, don’t make me think about that again – I just want them to be happy, and seeing how much pining is going on every time they’re near each other, getting them together seems to be the best way. Not to mention that watching them eye-fucking is downright gross sometimes. But yeah, I’ve left them alone in the room _so_ many times, and _nothing has ever happened_.”

Charlie sighed and leaned back, shaking her red hair back over her shoulders. “I mean, what did you expect? It’s not like they’re magically going to open up about their feelings for each other just because there’s no one else left in the room.”

“Exactly,” Jess agreed. “Someone’s going to need to give them a push. Now the question is, what’s that going to be?”

“Oh!” Jo exclaimed, suddenly sitting straight upright and looking around excitedly. “Guys, do you know what day Friday is?”

Charlie’s eyes widened in realization as Jess gasped. “Oh my God, it’s perfect!”

Jo squealed and jumped to her feet. “Guys, are we on the same page here?”

“Yes, absolutely.” Charlie grinned.

The three of them turned back to Sam, who was looking increasingly alarmed, and chanted in unison, “It’s going to be Valentine’s Day!” 

 

 

 

 

 


	2. Roses Are Red, Violets Are Blue, Would You Like Some Pie, Darling?

**Summary for the Chapter:**

> It's Valentine's Day, and Sam and the shipping trio are ready to put their plan into action.

 

 

Sam looked very disgruntled when Charlie delegated the task of giving Cas a push in the right direction to him, especially since it was five in the morning and he had wanted to sleep another hour, at least.

“What the hell am I supposed to do?” he demanded. “Sit him down and have a nice little heart-to-heart chat about his feelings for my brother?”

“No, silly,” Charlie laughed. “We have to be more creative than that. You’re the one who said that he’d disappear somewhere if we startled him like that, right? So you have to meddle, but you can’t let him _know_ you’re meddling. Not yet. We haven’t gotten that far.”

Sam rolled his eyes. “I’m a lot less competent at this than you think I am.”

“I have a very good idea of how competent you are at this,” Charlie retorted, miffed. “That’s why we’ve already come up with a plan _for_ you. You just have to be the one to do it.”

“Why _me_?” Sam complained.

“You know him better,” Charlie reminded him. “So, here’s the plan…”

 

 

Two hours later saw Cas squinting in confusion at Charlie as she walked past with a large, beautiful bouquet of mainly roses and a small wrapped box on her way to Jo’s room.

“Sam,” he said slowly. “Why is she carrying a gift and flowers? I’ve only seen such elaborate clusters placed at graves, or at a sick person’s bedside, but no one in this house is ill or dead.”

Sam snorted, flipping a page in his magazine. “Yeah, I’d hope not.”

Cas was still squinting at Charlie’s retreating form. “Then what are the flowers for?”

“It’s Valentine’s Day,” Sam said.

Clearly, that didn’t help. “Is it customary to carry flowers through the house on Valentine’s Day?” Cas asked.

Sam laughed. “No, not really. She’s bringing a present and flowers to her girlfriend. That’s the customary part.”

Cas’s eyes widened. “I see. So Valentine’s Day is a day to bring items to one’s significant other.”

“Well…yeah, for the most part,” Sam agreed, unable to believe he was having this conversation. They’d all expected Cas to know the gist of the holiday and Charlie was just there to serve as a reminder that it was indeed February 14, but clearly he didn’t. Sam shouldn’t have been surprised; Gabriel hadn’t come by to pay him a visit yet either, so he supposed all angelic beings didn’t place much value in trifle things like flowers.

“What’s the other part?” Cas pressed.

“It doesn’t _have_ to be a significant other,” Sam explained, still unable to believe that he was explaining Valentine’s Day to an angel. And then, suddenly, he knew _exactly_ how to put this situation to his advantage.

He closed his magazine. “It could be someone you like, even if you’re not in a relationship with them,” he said. “Say you have a crush on someone and you want to make their day a little better, you could get them something. Flowers, usually, though sometimes people throw in something else too that the other person likes. Or if you’re trying to flirt with them and they’re not noticing.”

Cas stiffened ever so slightly. “And these flowers symbolize…what, exactly?”

Sam shrugged, struggling to hid the grin pulling at the corners of his mouth and stay casual. Over Cas’s shoulder he saw Charlie, Jo, and Jess all clustered behind the doorframe leading to the hallway, Charlie giving him an encouraging thumbs-up.

“Depends on the color and flower. Usually people give roses. Some colors are for friendship, some for admiration, some for appreciation…and, obviously, some for love. Those are the red ones.”

“Ah. And…where would one obtain these flowers?”

Sam _really_ couldn’t hide the grin now. “At the local supermarket, I guess.”

“And are they expensive?”

“Not really, I guess, depends on how nice you want them to be. The better bouquets are bound to cost more.” Sam waggled his eyebrows and leaned towards Cas. “Why, is there someone you’re thinking of getting flowers for?”

Cas blushed and ducked his head to hide it. “Of course not,” he said, too quickly. “I was just curious.”

“Ah.” Sam opened his magazine again, knowing he couldn’t go too fast or he’d scare the angel off. He was pushing it pretty hard as it was.

There were a few moments of silence.

Then, very quietly, Cas asked, “Is it customary that these flowers be delivered in person?”

Well, shit. How the _fuck_ was he supposed to respond to that?

Sam took a deep breath. “Yeah. Yeah, that’s usually how it’s done.” He risked a glance behind Cas to see Charlie making a slightly scared face and shaking her head. Don’t push it too far.

“Or you could leave a note,” he added quickly, “if you’re not sure about giving it to them in person.”

“I see.”

Another few moments of silence.

And then, again very quietly, “Sam, may I borrow some money?”

 

 

Sam saw Cas walking hesitantly towards Dean’s closed door an hour later carrying a glorious bouquet of red roses and a freshly baked apple pie and quickly ducked back behind the doorframe. He pulled out his phone to text Charlie.

 

_He’s going to Dean’s room now_

The reply came just seconds later.

 

              _OMG!!! Keep us updated!!!_

Cas gently set the items outside of the door, pulled a small, folded piece of paper from his pocket and stuck it between two flowers, and made a hasty retreat as if he were afraid Dean would open the door and see him there.

As if. It was approximately eight in the morning. Dean wouldn’t be awake for another three hours, if he were following his normal schedule.

Sam quickly typed out a message.

 

              _He left a note – not sure what it says_

A few replies in quick succession.

 

              _Would it be wrong to check???_

_Safe to come out now?_

_No actually come to my room, we’re all here_

_Quickly!!!_

Sam looked around. Cas had already disappeared. He stepped out from behind the doorframe and went to Jo and Charlie’s room at the end of the hall, but not before taking a quick peek at the note Cas had stuck in Dean’s flowers. He grinned, and then reminded himself that he was _not_ shipping his brother with an angel. He was just tired of the eye-fucking. That was all.

“Did you check?” Charlie demanded as soon as he opened the door.

“Calm down,” Sam hissed. “We don’t want him to know we’re meddling yet, do we?”

“Sorry,” Charlie whispered, but excitement sparkled in her eyes. “But come on, tell us!”

“It was a bit vague,” Sam admitted. “But better than nothing.”

“Just tell us!” Jo begged. “What did it say?”

Sam pulled out his phone. “I took a picture.”

“You sneaky bastard,” Jess gasped, but she was smiling as she and the others gathered around Sam’s phone and read the note.

 

_As is custom to give flowers and a gift to those we care about on Valentine’s Day, I hope you enjoy the pie._

 

Charlie squealed. “Oh my _God_ , that’s _adorable_! Do you think he’ll get it?”

“Honestly speaking, he probably won’t, so don’t get your hopes up,” Sam sighed.

“We’ll see.” Jess looked determined. “We have plenty more ideas. We’ll get them together.”

“But…let’s say he doesn’t get it.” Charlie was abruptly serious. “We need to give him a nudge in the right direction too. Give him some clues that it was Cas.”

Sam’s eyes widened in alarm and he shook his head vigorously. “No no no. No way. You’ll scare Cas off for sure.”

“What if he’s not there, though?” Jo pointed out. “What he won’t know won’t hurt him.”

“Exactly,” Charlie agreed. “I agree we have to take it slow, but we have to do _something_. If he asks, we’ll just say we saw Cas buying flowers at the supermarket this morning.”

Sam raised an eyebrow. “‘We?’ All four of us?”

Charlie rolled her eyes and gave an exasperated sigh. “ _I_ saw Cas buying flowers at the supermarket this morning when I was getting some for Jo. Happy now?”

“Much better. But he might not ask.”

Charlie rolled her eyes again. “Honestly, Sam, I’m not surprised your meddling didn’t work. The solution is simple; we’ll just stage a conversation. One of us will ask Dean what the flowers were doing outside of his room, and then I’ll just slip in that I saw Cas earlier. It’s easy.”

“That’s perfect!” Jess exclaimed. “We can do it over lunch; Cas doesn’t really eat so he might not even be there, and Dean’s always so hungry that he’s not going to run away from us even if he feels awkward!”

Sam snorted. “I mean…yeah, true. Okay. Over lunch it is.”

 

 

As Sam had expected, they were almost done with lunch and Dean still hadn’t mentioned the flowers or the pie at all. He felt a kick under the table and looked up from his salad to see Charlie looking at him pointedly.

Now. Okay.

He cleared his throat.

“So, uh, Dean.”

Dean looked up from the magazine he was reading and answered with his mouth full of burger. “Yeah?”

Sam made a face. “Ew, Dean, that’s disgusting.”

Dean chuckled and swallowed. “It’s so fun to annoy you sometimes.”

“Yeah, yeah. Shut up. So what I was going to say was…”

“We saw some flowers outside of your door this morning,” Jess interrupted with a smirk and a mischievous glint in her eye.

Dean raised his eyebrows. “Yeah. I thought one of you had brought them in from when someone left it outside or something. The note didn’t have a name.”

Sam snorted and took a bite of salad. “Well, it certainly wasn’t me.”

Dean punched him lightly in the shoulder. “Now who’s being disgusting, huh?”

Sam gave him his second-best bitchface, his first already having been used against Jo a few days ago, but as his mouth was full of salad, he didn’t really have the grounds to argue.

Jo leaned forward eagerly. “Do you have a secret girlfriend?” she whispered. “Was it from her?”

Dean looked taken aback and almost dropped his burger. “What? No.”

Jo wasn’t fazed. “A secret _boyfriend_ , then?”

A very slight blush crept up Dean’s neck. “No.”

Jo’s grin widened. “You’re blushing.”

“I don’t have a secret boyfriend,” Dean said forcefully, his ears now reddening.

Jess took a sharp breath. “Oh, so you don’t have a _secret_ boyfriend, but you probably have a _crush_ , right?”

“This is a completely different topic,” Dean said loudly.

“He’s blushing!” Jo announced triumphantly. “Dean has a crush!”

Dean glared daggers at her, but, Sam noticed, didn’t deny it. Wow. Talk about miracles.

“Why didn’t you get flowers for him?” Jo pressed. “Or _did_ you?”

“I…” Dean began loudly, but then broke off.

“What?” Jo gasped. “You _did_?”

“I didn’t,” Dean snapped. “He’s –” He broke off again, realizing he’d just been about to give away that he did, indeed, have a crush, and settled for glaring dangerously around again.

“Okay, but really, who do you think left the flowers?” Jess asked. “Come on, let’s think. Who could it be? Could it be Dean’s crush?”

“Wait guys,” Charlie interjected. “Is Cas in a relationship?”

Dean almost choked. Sam pretended not to notice and said, innocently, “Um, I don’t think so, but I could be wrong. Why?”

Charlie frowned. “I saw him buying flowers at the supermarket this morning. Red roses.”

Jess’s eyes widened. “Like the ones we saw outside Dean’s door?”

“Well, I didn’t see Dean’s flowers, so I wouldn’t know,” Charlie pointed out sassily.

“Oh my _God_ , that would be _so_ cute!” Jess gushed. “I mean, everyone _knows_ how much he cares about Dean already, and to get him _flowers_ on Valentine’s Day? I love it!”

“It wasn’t him,” Dean interrupted abruptly.

Four pairs of eyes turned to him.

“How do you know?” Jo demanded. “You said there wasn’t a name on the card.”

“It wasn’t him,” Dean repeated. “He…he doesn’t do those kinds of things.”

Charlie snorted. “Are you calling me blind? I was literally there. I _saw_ him buy those flowers, Dean. I know it was him.”

“Well…they were probably for Meg or someone.”

Charlie raised an eyebrow at Sam, and the message was clear. _Meg?_ _Who the fuck is Meg? We’re going to have to talk about this._

Dean pushed his chair back and stood up. “Anyway, I have stuff to do. See you later.” He put his plate in the dishwasher with more force than was strictly necessary and left, slamming the door behind him. The Impala’s engine roared to life, and he was gone.

There was an awkward silence in which none of the four sitting at the table looked at each other. Charlie broke it with a frustrated exclamation.

“What the _fuck_ was that? Sam, who the fuck is Meg?”

Sam blinked. “I…I didn’t know she was still part of this! She had this thing for Cas a while ago, but it was never mutual. It was pretty obvious she was into him, but he never reciprocated. Like, ever. They haven’t talked for months, as far as I know.”

Charlie was practically fuming as she leapt out of her chair and began pacing around the room. “We were doing _so_ well! He was about to admit it, did you see? Ugh, I’m _so_ mad.” She huffed and sat back down. “Okay. Fine. We’ll work with it, we just have to change tactics, make Dean see that Meg was never in the picture.”

“Charlie, he knows they haven’t talked for months, and he _still_ thinks Cas is into her instead of him,” Sam pointed out.

“Don’t doubt me!” Charlie pointed an accusing finger at him. “We got you and Gabe together in less than a week, and we are _not_ going to fail this time.”

“It’s just a minor setback,” Jo agreed. “We’ll be back on track in no time. But as for now, we have to figure out a way to get Meg out of Dean’s head. From what I got, she’s pretty much the only thing in the way right now.”

Jess looked thoughtful. “You know, if Cas really isn’t into her, when someone mentions her name he shouldn’t have any kind of positive reaction. Kind of like if someone were to mention Sam in front of him – no offense, Sam.”

“None taken,” Sam muttered.

“Ooh yes, that makes sense!” Charlie was getting excited again. “Even if they were just friends, it wouldn’t matter! I don’t get all flustered whenever anyone randomly mentions Jess. But if someone were to have mentioned Jo before I got the balls to ask her out…well then, _that’s_ a different story.”

“So we just have to get Cas in Dean in the same room,” Jo began.

“That shouldn’t be hard, they’re literally always together,” Sam muttered.

“Shut up, Sam, I’m talking.” Jo slapped him playfully. “We just have to get them in the same room, and one of us will mention Meg in an offhand comment. It doesn’t even have to be _the_ Meg, just the name should do. And then we’ll just have Dean see that Meg means absolutely nothing to him.”

Sam sighed and put his head in his hands. “One very important thing that you guys are forgetting: Dean is _terrible_ at reading emotions.”

Jess groaned. “You’re right. We keep overestimating his ability to do that.”

Charlie sat forward. “Guys, we’re forgetting that _Cas got flowers for Dean_. That’s gotta mean something, right? He _wants_ this with Dean. I mean, they both want it, of course, but Cas is willing to do something about it. I…I think it’s time that we bring him into this.”

 

 

 

 

 


	3. Obvious

**Summary for the Chapter:**

> They bring Cas into the plan. Cas freaks out. Sam is an awkward shipper as always.

 

 

It was decided that only Charlie and Sam were to confront Cas about his quite obvious homosexual feelings towards Dean, since he would be less likely to freak out with fewer people and Charlie was the head of the operation. Sam was only there to make sure Cas didn’t freak out too much, since Charlie was a little overwhelming at times.

Cas appeared in the room moments after Sam called him. “Yes, Sam?”

“Hey, Cas. Um. How’ve you been?”

Cas squinted at him. “Sam, you saw me only a few hours ago.”

“Right. Yeah.”

“So.” Charlie sat forward and laced her fingers together. “First things first. You have to promise not to mojo yourself away from us.”

Cas hesitated. “Um. Okay.”

“Great!” Charlie grinned. “Sit down.”

Looking slightly apprehensive, Cas sat.

Charlie was still grinning. “Wonderful. Now, Sam, work your magic.”

Cas looked at Sam with alarm. “Magic? Sam, you did not tell me that –”

Sam groaned and covered his face with his hands. “Cas – Cas, no. Don’t take that literally. I don’t actually have magic. It’s just an expression.” He sighed. “Okay. So, uh. As for why we brought you here, I…I was just wondering…Valentine’s Day flowers?”

Cas blinked. “What about them?”

“You…uh. Who was…were you…oh, fuck it. I’m just going to say it. Did you get them for Dean?”

Pure panic flashed across Cas’s face and Charlie grabbed his arm tightly.

“No,” she said sternly. “You promised you wouldn’t disappear on us.”

Cas looked at Charlie, then at Sam, then back at Charlie, then back at Sam, his eyes wide. “I…”

“It’s okay,” Sam said quickly. “Just – just calm down, Cas, okay?”

“I…I didn’t…” Cas flushed, his eyes pleading. “Sam, _please_ don’t tell him.”

Sam hesitated. “Uh…”

“Why not?” Charlie cut in. “You like him, don’t you?”

Cas’s cheeks reddened and he ducked his head. He shuffled his feet awkwardly and wrung his hands together. “I…Dean and I have…a bond. And we…I care about him.”

“Yes, we all know, but you like him, right?”

“As…as a friend, yes,” he said desperately.

Charlie huffed. “No, I mean, you’re in love with him.”

Another flash of panic, prompting Charlie to hold onto his arm again and give him a warning look to remind him he wasn’t allowed to leave.

“I…” Cas trailed off, looking desperately at Sam for help.

“Is that a yes?” Charlie pressed.

Cas flushed. “I…I…”

“He’s not denying it,” Charlie said, shrugging at Sam.

Cas flushed harder and looked down at his feet.

“It’s okay, Cas,” Sam said, patting him awkwardly on the shoulder. “We’re not going to judge you or anything. We…we just need to, um, talk.”

“Talk?” Cas’s eyes widened.

“No, no, it’s not bad,” Sam said quickly, seeing the fear in Cas’s eyes. “We…we want to help you. Um. Help you and Dean. Get together. You know.”

“That’s why we suggested you give Dean the flowers,” Charlie interjected cheerfully. “We’ve been trying to get Dean to notice that you’re oh so very obviously in love with him, but he’s not getting the hint and we think we’re going to need your help.”

Cas’s eyes widened even more. “ _My_ help?” He looked back and forth between Sam and Charlie again. “Oh no, he doesn’t know, does he?”

Sam snorted. “My dumbass brick of a brother? Of course not. He couldn’t see it even if I told him straight to his face; he’s too much in denial.”

“I mean, he loves you too, of course,” Charlie interjected. “He just doesn’t see that you love him back and there’s a good chance he’d freak and bolt if we told him to his face.”

“Yeah. We need you to help us get it through to Dean that you’re in love with him. Just…just be more direct with him, Cas,” Sam said, awkwardly. “My brother’s as thick as a rock when it comes to emotions. You just gotta get it through to him.”

Cas frowned.

“Be more direct. To the point. Obvious. You know?”

“Yes, I know what that means,” Cas grumbled.

“Dean thinks you’re in love with Meg,” Charlie said loudly.

“I…I have no feelings for Meg,” Cas stammered, utterly confused, as was evident by the beginning of another squint.

Charlie grinned. “Exactly. And that’s what we need to get Dean to understand.”

Cas frowned even more. “How are we going to do that? One of you could simply tell him that I harbor no romantic feelings towards her.”

Sam sighed and rolled his eyes. “He’d only understand if it were coming from you, Cas.”

More panic. “No, I – I can’t tell him, I can’t talk to him about this, you don’t –”

“It’s okay, Cas,” Charlie said soothingly. “We won’t make you do anything you don’t want to do.” She flashed a knowing and mischievous grin at Sam before turning back to the angel. “Would it work better if you said it in an off-hand way? And not directly to him, but with him in the room? That way he’d hear it coming directly from you but you wouldn’t have to say it directly to him if you didn’t want to.”

Cas’s eyes brightened. “Would that…would that work?”

“With my brother, who knows,” Sam grumbled.

Charlie shot him a look and sat up, flipping her hair over her shoulders. “Of course it’ll work,” she said confidently. “He’ll actually be back soon, probably, which works perfectly.”

“We…we’re doing this _now_?” Sam hissed.

“Well, what is there to wait for?” Charlie shot back. “I’m trying to make record time here.”

Sam grumbled some more but conceded.

“So.” Charlie turned back to Cas. “Would that work? Would you be on board with that?”

Cas hesitated and then gave a slight nod. “Um. Yes?”

“Great! Just go along with what we say, okay? We’ll steer the conversation, and you just have to act natural and say that you really aren’t interested in Meg when we bring it up. Got it?”

“Um. I think so.”

“Wonderful.” A car door slammed outside.

Charlie sat up gleefully. “It’s time!” she announced. “Jo, Jess, get in here!”

The two other girls appeared instantly, having been waiting eagerly behind the doorframe for the past many minutes of discussion, and sat down on the couch next to Charlie. Cas eyed them suspiciously and anxiously but otherwise had no reaction.

“So. Cas,” Charlie said loudly. “It must be really hard going out looking like that.”

Sam raised his eyebrows.

“Yeah, right?” Jo agreed, leaning forward to rest her elbows on her knees. “Jeez, you’re one gorgeous angel. You must get all the ladies.”

“And the men,” Jess chimed in. “Don’t be heteronormative now, ladies.”

Charlie tsked.

“Oh, I’m so sorry,” Jo said sweetly as the door opened, announcing Dean’s arrival. “My mistake; I just assumed since that girl was hitting on you earlier.”

“What girl?” Cas asked, utterly confused.

“Just go along with it,” Charlie hissed out of the corner of her mouth.

“I am,” Cas hissed back.

Sam was completely confused, but he saw an impressed look on Charlie’s face and decided that she had probably understood what was going on and he needn’t worry about it, so he sat back and took out his phone to scroll through the news so Dean didn’t become suspicious that he was partaking in girl gossip.

“The girl at the bar earlier?” Jess asked, raising an eyebrow. “Don’t tell me you forgot about her already? You even bought her a drink!”

“Hmm, what was her name?” Jo mused. “Molly? Mary?”

“Meg,” Charlie quipped, just as Dean came into the room. Out of the corner of his eye, Sam saw his brother’s face go stone cold.

“Oh, Meg, right,” Cas said blandly. He glanced at Dean. “Hello, Dean.” Sam saw the effort it took him to remain casual.

Dean gave a noncommittal grunt, standing stock-still.

Jo leaned forward some more. “Well? What did you think of her? Oh, she was _all_ over you.”

Cas sniffed, as Sam saw Dean’s face go from more-or-less neutral to positively thunderous.

“I didn’t like her,” Cas said dismissively.

“What!” Charlie exclaimed. “She’s your ex, right? I mean, she sure made it sound like she was.” She gasped. “Ooh, was she trying to get back with you? Is that what she wanted? Damn, Cas, was she hot!”

“We never dated,” Cas replied, still completely dismissive. “She liked me, that was all. It was never mutual.”

“Not at _all_?” Jess pressed. “Not _one bit_?”

“Never.” Cas squinted. “I was never interested in her, and I never will be.”

Out of the corner of his eye, Sam saw Dean relax. The shipper in him cheered before Sam realized what he was doing and reminded himself that he was _not_ shipping, just tired of their eye-fucking everyday.

Charlie gasped again. “Oh, is there someone else you’re with right now?”

Cas looked offended. “What kind of person do you take me for? If I were with someone else and going to a bar, that would make me a cheater!”

“Oh, so you’re single,” Jo clarified.

Cas shot her a look. “Obviously.”

“So…single and not into girls like Meg,” Charlie mused. “Damn, you’re picky.”

“I just have different tastes,” Cas sniffed, and Dean relaxed enough to continue his walk through the room and head to the kitchen.

Charlie waggled her eyebrows as soon as he disappeared. “That was so great, guys,” she whispered excitedly. “He got the message, did you see? As soon as he heard Cas was single and not into Meg, he relaxed and left.”

“Do you think this is going to be it?” Jo asked.

“Seems like a good a chance as any,” Jess said. “But it’s Dean, so you never know. We’ll just have to wait and see if he does anything about it.”

Charlie nodded. “I agree. We’ll give him a few days, and if nothing happens, time for our next plan.”

 

 

 

 

 


	4. ...More Obvious?

**Summary for the Chapter:**

> Charlie, Jess, and Jo have a new collective nickname: the Shipping Girls. They go forth with their next plan - will Dean get it, or will it take more for him to confront his feelings about Cas?

**Notes for the Chapter:**

> Thanks for all the support guys! Sorry it took me so long to update!

 

 

Dean, not surprisingly, did not get it.

Charlie waited for about a week to see if Dean would actually do something, such as talk to Cas about their feelings for each other, but she didn’t see any changes in their interactions and figured it didn’t happen. She and what Sam had now started calling the Shipping Girls gathered him and Cas around in them in Charlie’s room the next Wednesday morning.

“Cas, I think it’s safe to say that Dean hasn’t done anything,” Charlie said.

Cas frowned. “No. He hasn’t.”

“Is that supposed to be surprising?” Sam muttered. (He still didn’t believe he was doing this. But it was just for his own good, okay? He was _not_ part of the Shipping Girls; he was not a shipper and he was _definitely_ not a girl. Even if his hair sometimes made it look like he was.)

Charlie poked his shoulder. “No, silly, but that’s what we’re trying to change!” She groaned and threw her hands up in the air in frustration. “I don’t get it. How much do we have to do for him to actually get the hint and _say_ something? Is he really _that_ emotionally constipated?”

Jo snorted. “Jeez, you really underestimated him, Charlie.”

Charlie let out a dramatic sigh. “I know, I know. But how was I to know? Anyway, we have to think about what we’re going to do next. I wanted to get this done in record time, guys! But it’s been a week and nothing has happened, so I’m getting kind of desperate now.”

“Maybe Dean just needs to get jealous,” Jess suggested.

“He was jealous of Meg and look where that got us,” Sam pointed out.

“Yes, but Meg’s a girl,” Jess shot back. “Maybe he needs to get jealous of a guy.”

Charlie brightened. “Wait, Jess, you might be right! I mean he already knows that Cas isn’t into Meg and never was and never will be, and he knows that Cas is single. He also knows that Cas has ‘different tastes,’ so maybe he just needs to know what exactly those tastes are before he feels safe enough to make a movie.”

Cas spoke for the first time. “Isn’t that going to be too obvious?” He sounded quite apprehensive. “I can’t just say it to his face that I find men with brownish hair and green eyes attractive, you know.”

“No,” Charlie conceded, “but we could do something like we did last time where he was in the room while you were talking about it.”

“That’s _still_ going to be obvious,” Sam grumbled. His phone buzzed and he pulled it out of his pocket.

Charlie shoved him. “Sam, pay attention, this is important!”

“No, _this_ is important,” Sam insisted, showing her the screen. “It’s Dean. Can’t just ignore my brother, you know.”

The Shipping Girls all immediately crowded around him to see the message.

 

              _Headed out. You guys need anything?_

“Oh, that’s boring,” Charlie said dismissively, sitting back again.

Sam hmphed and typed out a quick message to let Dean know that they were fine before slipping the phone back into his pocket. “Anyway, what were we talking about? Making Dean jealous of a guy?”

Charlie nodded.

“So…this would work better if the guy actually _looked_ like him, right? I mean, if Cas pretends to have a crush on a guy with dark hair and brown eyes, Dean’s going to think those kinds of guys are Cas’s type. He should do it with some typical hot blond dude.” He winced as he said that. “Hot blond dude” were never words he wanted to use when talking about his brother.

“Wait, he has a point,” Jess said.

Jo frowned. “Yeah, I see it, but where are we going to find that kind of opportunity? I mean, we can’t just pick up a random magazine and point out hot blond guys, right? That would be hella suspicious.”

“We could do it with a movie?” Charlie suggested. “Cas, what do you think?”

“I have never watched a movie except for the one about the pizza man,” Cas said.

Charlie looked at him, utterly confused, and Sam choked.

“No, Cas, that’s not…that’s not what we’re talking about,” Sam managed.

Charlie turned her raised eyebrows on Sam. “What movie about the pizza man?”

Sam felt his cheeks heating up. “It…it was porn.”

Charlie stared at him for a few very long moments before abruptly bursting into laughter. “Oh my God, really? You guys watched _porn_ together? Sam, I expected better of you! At least you could’ve suggested Dean show him the ropes about sex?”

Sam choked again and winced. “No, stop, I _really_ don’t need that image in my mind. And no, we were not watching porn together, that’s gross! Cas here just had it playing on the TV and we happened to be in the room.”

“Anyway,” Jess interrupted. “Get back to the point. We need to figure this out before Dean gets back, otherwise he’s going to hear us all crowded in this one room and be even more suspicious about what we’re doing.”

“Okay. Right.” Charlie clapped her hands together and turned back to Cas. “So we were talking about making Dean jealous with a movie.”

Cas gave an uncertain nod. “…Yes?”

“Is that a yes, that’s what we were talking about, or yes, we should do it?”

“Both.”

Charlie whooped. “Great! So we know what we’re doing! What movie should we watch?”

Jess blushed. “You know…I’ve always thought Chris Pine was pretty hot. We could watch _Star Trek_? Gives off plenty of vibes about man-on-man love too, maybe it’ll give Dean the right idea.”

Sam looked around, confused. “Man-on-man love? I thought it was about exploring space?”

“Kirk and Spock, silly,” Charlie laughed. “I mean, it’s all subtext right now, but it’s pretty damn obvious subtext, so maybe Dean will still be able to get it.”

“But we still have to convince Dean to watch it with us,” Jo pointed out.

“Oh, don’t worry, he’ll watch it,” Sam assured them. “He’s pretty nerdy in his own way. _Star Trek_ is something that he’ll definitely want to watch, even if he doesn’t sound like he’s excited. I know my brother, guys.”

Charlie grinned mischievously. “This is _so great_! He _has_ to get it after this, I mean how hard would it be to put it together? Cas doesn’t like Meg, he’s single, and now he’ll know that he’s into guys with blond hair and nice eyes…basically spelling it out for him.”

“We’ll try it out and see how it works,” Jess said. “Cas, what do you think?”

Cas shifted uncomfortably as four pairs of eyes turned to him. “Um. Yes, I think it’s worth a try, but –”

Charlie looked pleased. “Wonderful. Now we just have to wait for Dean to get back and then we can start the movie!”

“Wait,” Cas interrupted. “Dean informed me that it is…improper to watch such movies with other men in the room. Would this be an issue?”

Sam cleared his throat uncomfortably as the Shipping Girls snorted. “Um, no, that’s just…that’s just with porn, Cas. This isn’t the same thing, trust me.”

Cas blinked. “Oh. Okay. Then yes, I agree with this plan.”

Charlie grinned and stood, pulling Cas to his feet. “Great! Now we’ll just have to wait for Dean to come back, and then we can start the movie! I promise, you’ll have your man before long. Just make sure that you play along with us, okay? You have to make it clear that you fancy Chris Pine and then Dean will get super jealous and then everything will work out!”

Cas looked slightly unsure, but he let Charlie drag him into the living room and sit him down in front of the TV. Sam followed along awkwardly, sitting down in a chair off to the side.

“Any idea when he’s planning to be back, Sam?” Jo asked as she settled down next to Charlie and lay her head on her shoulder.

“Nope. No idea. Knowing him, he’s probably out getting pie or beer or flirting with some hot girl to ease his butthurtness about thinking Cas doesn’t like him.”

Cas frowned. “I don’t like the idea of him flirting with some hot girl.”

“All the more reason to follow through with this,” Charlie quipped.

The sound of the Impala’s engine rumbled in the driveway.

“Looks like you were wrong,” Jess said, grinning. A few moments later, Dean walked in the door carrying several bags, a large pie, and another large plastic bag that looked like it was full of beer bottles. He saw them all sat around the TV and raised his eyebrows.

“What’s going on here?”

“We’re watching Star Trek!” Charlie announced cheerfully. “We thought you’d like to watch, too, so we were waiting for you to come back!”

Dean set the bags down on the table in front of them. “Well, uh, thanks, I guess. Which one are you guys watching?”

“Not sure, one of the new ones though. Maybe the newest one that just came out like last year or something? _Beyond_ , I think it was. Or do you have a preference?”

Dean shook his head, pulling what was indeed a bottle of beer out of the plastic bag and sitting down, to the Shipping Girls’ barely concealed excitement and Cas’s embarrassed delight and Sam’s _definite_ indifference, next to Cas. “Doesn’t matter to me. I brought you guys lunch, even though Sammy here said you guys didn’t need anything. The pie is mine, though.”

“Yeah, we figured,” Sam muttered, reaching for one of the bags of food and opening it. He let out a sigh and gave Dean a look. “Really, Dean? Burgers and fries?”

“That’s not yours,” Dean said, snatching it back and handing it to Cas.

Sam raised his eyebrows, looking back and forth between Dean and Cas.

Dean gave him a look. “What?” he demanded. “Cas likes burgers. Right?” Suddenly worried, he looked over at Cas. “Right? You like burgers?”

“What? Oh – oh, yes, I love burgers,” Cas said, taking the burger out of the bag and enthusiastically taking a large bite of it.

Dean looked back at Sam, a pleased grin on his face. “See?”

Sam rolled his eyes. “Okay, okay, whatever. So where’s mine?”

Dean handed Sam another bag. “Figured you’d appreciate a salad more than a burger, so that’s what I got you. Fork’s in the bag.”

Sam brightened, ripping open the bag and digging into his salad as Dean distributed the rest of the food to the Shipping Girls. “Honestly, I don’t see how you survive on just salad, considering how much pointless running around you do.”

“It’s _not_ pointless,” Sam countered, offended. “It keeps me healthy. Exercise is good for you.”

Dean snorted and leaned back with his pie. “Whatever.”

“Anyway, it’s about time to start the movie now, right?” Charlie said cheerfully as she ripped open a packet of ketchup and drizzled it over her fries. “Dean, could you put the DVD in?”

Dean gave her a look. “Really, Charlie? I _just_ sat down, _and_ I’m the one who got you food.”

Sam sighed dramatically and stood up. “I’ll do it. Lazy ass,” he muttered, shaking his head as he turned on the TV and bent to put the DVD into the player. “Okay, we’re watching _Beyond_. If anyone has an issue with that, speak now or forever hold your piece.”

No one protested, so Sam sat back down and waited for the movie to begin.

Jess let out a loud sigh as soon as Captain Kirk appeared on the screen. Dean looked over at her with his eyebrows raised.

“Oh, he’s _so_ handsome,” Jess gushed. “Oh my God, just look at his _eyes_ , they’re so beautiful! Wish I could find me a man like that.”

“Shut up and watch the movie,” Dean grumbled. “It’s Star Trek, not one of your chick flicks.”

“You love chick flicks,” Sam said.

Dean gave him a glare, but couldn’t think of a good reply, so he took a large bite of pie instead and looked back at the TV.

They sat in relative silence for some time, eating lunch and enjoying the homoerotic subtexts between the captain of the _Enterprise_ and his Vulcan friend, Charlie occasionally commenting that she really thought Chekov and Sulu should’ve ended up together if Sulu weren’t already married, even though the main developing relationship in the movie was, of course, between Spock and Kirk.

“You know, I get that Vulcans are supposed to be all no-emotion and cold and stuff, but Spock isn’t really against dating, you know?” she said. “I mean, yeah, he broke up with Uhura, but he _dated_ Uhura. He’s perfectly fine with romance. And now that he and Uhura broke up, he really should go with Kirk; they’re clearly in love with each other.”

“Funny how all of the best couples are one blond quirky one, one dark haired mysterious one,” Jo mused. “I mean look, Sherlock’s the dark mysterious one and Watson’s the blond quirky one, Lexa’s the dark mysterious one and Clarke’s the blonde quirky one, Spock’s the dark mysterious one and Kirk’s the blond quirky one…”

“Blond quirky _hot_ one,” Jess added.

Jo hummed in agreement. “He really is wonderful, isn’t he?” She turned to Charlie. “Don’t you think so?”

Charlie held up her hands. “Hey, don’t look at me, _I’m_ gay.”

They looked at Sam.

Sam blinked. “Huh? What are you looking at me for? Y’all know I’m seeing someone already, I can’t go complimenting someone else’s man.”

Everyone looked at Cas.

Cas swallowed uncomfortably. “Oh.” He blushed. “Yes, he’s quite…quite a sight to look at.”

Charlie gasped and bounded over to sit on his other side, cuddling up next to him. “Ooh, wait, you said you had different tastes, right? Is he your type? Dirty blond hair and beautiful eyes?”

“I prefer men with good personalities,” Cas said loftily. “Physical features will change with age.”

“Oh, come on, there _has_ to be a certain type of guy you’d like to fuck.”

Cas ears turned pink. “I…well, I guess…”

Sam noticed that beside Cas, Dean had stopped chewing, his cheeks bulging with a mouthful of pie, his eyebrows halfway up his forehead.

“Oh my God, this is so beautiful!” Charlie gushed. “Look, Jo, your theory is _so_ right!” She ruffled Cas’s hair affectionately. “Dark hair, mysterious, likes quirky blond guys with good personalities…” She leaned in more. “Oh my God, Cas, do you have someone particular in mind?”

Cas’s face was thoroughly red. “I…um…sort of, yes,” he mumbled.

Jo squealed and leaned forward eagerly. “Who is it?”

Cas looked slightly panicked. “Um, I…” His eyes flashed in Dean’s direction before looking away just as quickly. “I don’t…”

“Guys, leave him alone and watch the movie,” Dean sighed, sounding much more stiff than Sam was used to. “While y’all are trying to figure out who Cas has got a crush on, _I’m_ trying to actually hear what they’re saying. I don’t trust this Kalara chick here.”

Cas looked greatly relieved. “Yes, I agree with Dean, she does not sound trustworthy.”

Charlie sat back, disappointed. “Aw man, Cas. Pleease?”

Cas shook his head forcefully. “He has dark blond hair and beautiful eyes and has a wonderful personality. That is all you need to know.”

“You know,” Charlie mused, “ _Dean_ here has dark blond hair and beautiful eyes and a wonderful personality…”

Cas looked utterly panicked, and Dean stood up abruptly and left.

Sam looked at the Shipping Girls, utterly bewildered. “I thought it was going well,” he said. “We were going pretty obvious.”

Charlie looked confused. “Yeah, I thought so too.” She frowned. “But Dean just…it’s like he doesn’t want to hear it. Not that he doesn’t love you,” she said quickly, seeing Cas’s face crumple. “He loves you, don’t worry. I think he’s just…I think he’s just scared to admit it.”

Jo gasped. “Wait, Charlie…I think I know what the problem is. It’s that he’s been hearing it from us. When we tried to tell him that we saw Cas buying flowers, remember how he reacted? He refused to believe that he wasn’t buying them for Meg. And now, hearing from us that Dean looks _exactly_ like Cas described his type to be?”

“But when _Cas_ said he wasn’t interested in Meg…” Charlie’s eyes brightened. “I think you’re right! He believes it coming from Cas, but from anyone else, he just thinks they’re messing with him.”

“That’s it,” Charlie declared. “I know what we have to do. We have to find a way to make Dean realize that Cas loves him by making _Cas_ say it.”

“No,” Cas said abruptly. “No, I – I can’t do that.”

“It wouldn’t be direct,” Charlie assured him. “It would be kind of on the side, the way we’ve been doing. And it’ll work, trust me.” Her eyes glinted. “I have _just_ the right idea.”

Sam arched his eyebrow. “Which is…?”

Charlie grinned devilishly. “We’re playing _Marry, Fuck, Kill_. And if that doesn’t work?” She leaned forward and lowered her voice. “ _Cards Against Humanity_.”

 

 

 

 

 


	5. Cas Has a Hard Time Not Taking Things Literally

**Summary for the Chapter:**

> They play 'Marry, Fuck, Kill.' Things get honest. People get flustered.

 

 

“I don’t understand,” Cas said as they all sat around in a circle two days later, Dean and Gabriel included. Gabriel had come only because Sam had asked him to and was now perched on the backrest of the couch, purposefully annoying Sam by putting his feet on Sam’s shoulders. “I don’t want to have sex with or marry any of these options. Two of them are fictional characters and the other is a demon.”

“That’s okay,” Charlie said with a grin. “It’s all hypothetical. If you had to marry, fuck, or kill each of the people I told you, what would your preference be?”

Cas frowned. “You said Crowley, Dolores Umbridge, and…who was the third one?”

“Gollum from _The Lord of the Rings_ ,” Charlie said immediately.

“I don’t want to have to have sex with or marry them though,” Cas said.

“No, you don’t _have_ to, not in real life,” Charlie said. “As I said, it’s hypothetical. Given a situation where you had to, what would you pick? C’mon, it’s just for fun.”

“Oh.” Cas’s frown deepened. “Well, I do not know much about Dolores Umbridge and Gollum,” he said. “But I would certainly not want to marry or have sex with Crowley. So that means I would kill him,” he concluded with a pleased nod.

“And who would you fuck?” Gabriel asked with a smirk.

“Based on the information Charlie has provided me with, Dolores Umbridge would prove least likely to try and violently bite my genitals off. Therefore, I would have to have sex with Dolores Umbridge and marry Gollum.”

Charlie snorted a laugh. “Ew, that is _so_ gross.”

“You’re the one who picked them,” Dean pointed out, smirking. “Cas fucking a weirdo sadistic pink toad lady. What a sight.”

Gabriel shot him a look. “I did _not_ need that imagine in my mind, thank you very much. Now where do you keep your bleach? I’d like to wash my eyeballs with it, please.”

“Shut up, Gabe,” Charlie laughed. “It’s your turn now anyways.” Her eyes glinted with mischief. “Anyone have some good ideas? Are we going gross or great? I’m thinking gross, right? I feel like that would be funnier with him.”

“Ooh, I have a good one!” Jess exclaimed. “A vampire, a rugaru, and evil Santa.” She grinned, pleased with her selection, as Gabriel’s face contorted into an expression of disgust.

“Now that’s just mean,” he complained. “Sam, why did you drag me into this?”

Sam shrugged, feigning innocence despite being thoroughly amused. “You’re the one who agreed to it, so there’s no backing out now. Answer the question.”

Gabriel let out an exaggerated groan. “Fine. Uh…Chuck, this is hard. Damn. Okay, uh, fuck the vampire, marry Santa, kill the rugaru.” He made another face, as if he had just eaten something bitter. “Ew. Marrying Santa was definitely _not_ on my bucket list. But maybe he can give me sweets.” He said this with a pointed look in Sam’s direction.

“Hey, what are you looking at me for?” Sam demanded. “I got you gummy bears last week, didn’t I? You’re the one who never showed up on Valentine’s Day.”

Gabriel shrugged and sniffed. “Whoops, my bad. Your turn now, kiddo.”

“Pre-betrayal Ruby, Anna Milton, or Bela?” Dean asked immediately.

“Wow, you really were prepared for that,” Charlie commented.

“Aw, man, that’s easy,” Sam smirked. “Fuck Bela, marry Anna, kill Ruby.”

“Aha!” Dean’s eyes glinted in triumph. “So you _did_ have a thing for Bela.”

“I – what?”

Gabriel looked put-off. “What? Sam, is there something I should know?”

“Shut up,” Sam mumbled. “It was nothing.”

Dean smirked and leaned over to punch his brother in the shoulder. “We had to ask Bela for help this one time, and I could’ve _sworn_ Sammy had a wet dream about her, he had the weirdest look on his face when she showed up and he tried to say it was nice to see her and ended up mixing up his words, it was hilarious. Never admitted it, though, but I guess there’s no need to now.”

Sam groaned and rolled his eyes, feeling his neck heating up with a blush. “Come on, Dean, that was _years_ ago. Can we let it go already?” He turned to Jo as Dean chuckled and got up to get a beer. “Your turn now. Anyone got any good ideas?”

Charlie’s eyes glinted in mischief. “Yeah, _loads_. Alright, girl, Chris Pine, Emma Watson, and Sofia Boutella.”

Jo’s eyes widened in dismay. “What? That is _so_ not fair.” She sighed. “Alright, alright. Jesus, this is going to be _so_ difficult. Um…damn, they’re all so beautiful. I don’t want to kill _any_ of them…” She trailed off with a frown. “Okay,” she said finally. “I think I got it. I _really_ don’t like killing them, but…I think I’d marry Emma. She’s so smart, and kind, and such a feminist…doesn’t get much better than that, really. And then…aw man, I really don’t want to kill Chris, but I’m more gay than I am straight, so I think that’s what it’s gotta be. Marry Emma, fuck Sofia, kill Chris.” She sighed. “Sorry, Chris. Love you.”

Jess made a face. “Aw man, it’s my turn now, isn’t it? Please have mercy, guys.”

“Not a chance.” Charlie grinned. “Tom Hiddleston, Sam, and Dean.”

Sam gawked. “What?”

Cas’s eyes widened in alarm. “What?” he seconded.

Dean had just returned with a beer and had taken a large swig of it; he choked, narrowly missing spraying everyone in the face. “What?” he echoed.

Charlie threw her head back in what Sam thought quite frankly was an evil laugh at their expressions. “You heard me. Tom Hiddleston and the Winchester bros.”

Jess shook her head adamantly. “No no no. No way. Asking me to choose between a childhood friend and Tom Hiddleston? That’s just not fair. Sam doesn’t stand a chance. No offense, Sam.” She grinned at his offended expression. “I just can’t fuck you, that’s just too weird.” She made a face. “Can’t marry your brother since I think _someone_ would be all up in my face about it, and anyway Tom seems so delightfully sweet and kind that I think he’d be the best marriage partner anyway. So, uh, that means fucking Dean and, um, killing Sam. Sorry, buddy.”

“Great. Nice to know you love me too,” Sam muttered.

Dean had a very self-satisfied expression on his face. “It’s true, though. I’d rather fuck me, too. Who’s all up in your face about marrying me, though?” Beside him, Cas looked like he had been petrified.

Charlie and Jess exchanged a glance. “Not telling,” Charlie said, and Cas relaxed. “Though you should be able to figure it out pretty easily, considering all the clues they’ve been giving you. I’m surprised you haven’t figured it out already, really.”

Dean raised his eyebrows, looking at Charlie, then at Jess, then back at Charlie. “What?”

Charlie groaned and shook her head. “Oh, never mind. Let’s just get back to the game. Whose turn is it now?” She looked around and her eyes widened in dismay. “Oh crap, it’s mine.”

“Yeah, and I’ve got a good one,” Dean said. “Chuck, Percy Weasley, and that guy you pretended to flirt with to get into the office a few years ago.”

“The guy I pretended to flirt with? You mean the guy you _taught_ me how to flirt with?” Charlie smirked.

Dean’s mouth opened, hung open for a moment, and then closed. “That wasn’t ever supposed to come up again,” he hissed finally, completely oblivious to Cas’s shocked look and Sam and Gabriel’s snorted laughs.

Charlie shrugged, still smirking. “You’re the one who brought it up. And you kinda deserve it, for giving a gay all male choices.” She pouted.

“That was the point,” Dean said, taking another swig of beer.

Charlie sighed. “Alright, let me just get this over with. It’s not actually that hard, really; I may be gay, but I can still appreciate good looks in the opposite gender, and I _definitely_ can see what would be good for connections.” She grinned and pulled her hair back into a ponytail. “So. Marrying God would be pretty fucking awesome, and Percy’s not too shabby to look at, and I have no idea who the other guy is, so I’d probably kill him. Sorry, dude. I know you’re innocent.” She gave Dean a wicked grin. “Now I get to get back at you.”

“Oh, crap,” Dean muttered. “I’m regretting this already.”

“Oh, don’t worry, I’ll take it easy on you,” Charlie grinned.

Jo leaned over and whispered something in Charlie’s ear, and Jess leaned over to listen. Sam, who was sitting nearest to them, heard Cas’s name. A moment later, all three of them straightened up with pleased grins, and Dean’s eyes flickered over all of them apprehensively.

“Alright,” Jo said. “Anna, Lisa Braedon, and Cas.”

Cas’s face went white, and Dean went stock-still. Sam stared at the Shipping Girls in alarm, looking particularly hard at Charlie. It was too far. Dean would _flip_.

“Um. Well, uh…screw you, Charlie,” Dean muttered, his face thoroughly red. “Do I have to do this?”

“Yes,” Charlie said. “You agreed to play, so you gotta play! Now what’s it gonna be?”

Dean ran a hand through his hair, flustered. “Okay, okay. Uh, well I guess I’ll kill Anna, I know her the least out of the three. Slept with her once, but uh, just not the same as Lisa. So that means I have to fuck Lisa, and, uh…yeah, I’d marry Cas.”

Cas blushed and ducked his head, and Charlie leaned forward eagerly. “You’d marry Cas?”

“Well, uh, yeah, I’d marry Cas, that’s what I said, right?”

Cas’s ears looked _quite_ red, and Gabriel leaned over and punched his shoulder. “Someone’s embarrassed, aren’t they?”

Cas just mumbled something unintelligible and shook his head.

“Alright, Cas, it’s your turn again,” Jess announced. She looked around at the other two Shipping Girls. “Are we going gross or great with him?”

“Let’s go great,” Jo sad. “Right back at you, Cas. Sam, Dean, or Adam?”

Panic flashed across Cas’s face, but to his credit, he didn’t disappear. “Oh. Well, um…I…I guess would reciprocate Dean’s interests and…and marry him, and I would…have sex with Sam, leaving me no other choice but to kill Adam. My apologies to the youngest Winchester brother.”

He didn’t look at Dean, and Dean was too busy being embarrassed to look at Cas.

“Aw, that’s so cute,” Jo gushed.

“I think I’m _prime_ marriage material,” Sam muttered.

Cas squinted at him. “Dean and I share a more profound bond,” he said. “Is marriage not a more profound bond than the physical act of joining two bodies together?”

“People have sex when they get married, too,” Gabriel said casually, all the while looking slightly disgusted at picturing his brother in the act. “So yeah, I’d say that marriage is basically sex plus more. A.k.a. a more profound bond, which is what, apparently, Dean and Cas –”

Oh, fuck, Sam really did _not_ want to have this discussion. “Alright, alright,” he yelled. “I get it. Let’s move on now, shall we?”

“Nope.” Gabriel sat up promptly. “It’s my turn next and I have no interest in trying to choose between three very unattractive people again when I have a hottie right here who I can fuck right now. Let’s go, Sam.”

Sam turned bright red and Dean burst out laughing. “Go get it, Sammy.”

“Shut up,” he muttered, ignoring the pleased smirks on the Shipping Girls’ faces. He stood and followed the archangel out of the room.

“Damn, someone’s about to get lucky,” Jess smirked. She turned to Jo. “Well, now that they’re both gone, it’s your turn again. Me, Charlie, Dean.”

Dean gaped. “Why am I always in these?”

Jess shrugged, a self-satisfied smile spreading across her face at Dean’s expression. “It’s more fun when people here are involved, you know? Brings out what people really think of you. Like you and Cas, both saying you’d marry each other, you know? Stuff like that.”

Dean blushed. “Shut up. That’s nothing, it’s just a game.”

“You keep thinking that, sweetie. Now Jo, any idea yet?”

“Yeah. I have to marry Charlie, but you knew that. You were _really_ testing whether I’d choose you or Dean, right? Well, sorry Dean, but I think I’m going to have to kill you. Like I said, I’m more gay than I am straight, and as beautiful as you are, I can’t make exceptions.” She grinned.

Dean mumbled something under his breath.

Charlie looked around. “I’m getting bored of this, guys. Are you all up for Cards Against Humanity?”

“I do not know what that is,” Cas said.

“It’s okay,” Charlie said. “We’ll explain it to you. It’s super fun, though, I promise.”

Cas hesitated. “Dean, will you be joining us?”

Dean looked surprised. “Oh. Uh, well, yeah, I guess. It’s a cool game. Full of innuendoes, should be pretty entertaining.” He waggled his eyebrows.

“Okay,” Cas said. “Then yes, I am up.”

 

 

 

 

 


	6. Most Obvious

**Summary for the Chapter:**

> "Just…just be more direct with him, Cas," Sam said, awkwardly. "My brother’s as thick as a rock when it comes to emotions. You just gotta get it through to him."
> 
> Cas takes his advice to heart.

 

 

Charlie, of course, was the one with the cards. She dealt out ten white cards to each person as she explained how the game worked to Cas and put the rest of the white cards face-down in a stack on the ground. She pulled the black cards out of the box, made sure they were all facing down, and put them in a stack next to the white cards. “Alright, guys, who pooped most recently?”

“That’s not fair,” Dean complained. “Angels don’t poop.” He stopped and turned to look at Cas with a frown. “Do they?”

“Not in our true forms, no, but our vessels are still human. When we eat, we must also poop,” Cas explained calmly with a completely straight face.

“That’s still not fair,” Dean said. “Cas hasn’t eaten since we had lunch two days ago.”

Charlie groaned. “Oh, alright, alright. I mean we _could_ just rock paper scissors it but that’s boring. It’s Cards Against Humanity. It’s gotta be fun and a little bit dirty.”

Dean made a thoughtful face. “Well, pooping _does_ fit into that category.”

Charlie snorted a laugh. “Ew, Dean, that’s gross.”

Cas squinted. “Dean, I ate a pizza last night as well while you were sleeping.”

Dean blinked. “What? Did Jimmy have a weird craving or something?”

“I wanted to know what it tasted like.”

Dean stared at him. “So…so you’re telling me, you’ve _never_ had pizza before?”

“Correct.”

“Oh.” Dean blinked again. “Wow. We really gotta introduce you to some more food, then.” He turned to look back at Charlie. “Good thing is, though, we can still use the pooping thing to figure out who starts with the black card. I pooped when I woke up at two, anyone later than that?”

Everyone stared at him blankly.

“Jeez, you _really_ do wake up late,” Charlie said finally.

Dean shrugged. “I have to get my beauty sleep. Take advantage of sleeping in when you can, you know?”

Charlie just shook her head. “Well, I guess you’re starting with the card, then.”

Dean grinned and picked one up from the pile of black cards. “You have my sword. And you have my bow. And _my_ …?”

Jo pursed her lips as she flipped through her cards, putting one down casually and taking another white card from the larger stack to add to her hand. Charlie made a face as she looked back and forth between three cards, finally deciding on the third. Jess shrugged and put hers down without much fuss.

Cas looked thoroughly confused, putting a card down slowly with a very worried face.

Dean picked the cards up and shuffled them before he laid them out, face-up, in front of him. A grin spread across his face as he read through them. “You have my sword. And you have my bow. And my grandma.” He snorted. “Alright, that one is odd, I’ll give you that. Next one: you have my sword. And you have my bow. And my poor life choices. Okay, that’s a little _too_ relatable.” He moved onto the next two cards. “You have my sword. And you have my bow. And my powerful thighs.” He stopped. “Okay, dear Jesus…” He rolled his eyes up to the ceiling, feigning a prayer. “Last one,” he said finally. “Let’s hope we don’t need to atone for our sins after this one. You have my sword. And you have my bow. And my fiery poops.”

Charlie burst out laughing.

“Well, I guess there’s no need to guess who that one belongs to,” Dean muttered. “But sorry, Charlie, I have to go with powerful thighs. Whose was that?”

Nervously, Cas raised his hand.

Dean stared at him. “ _Damn_ , Cas, revealing a side of you I never knew existed. Here.” He passed the card to the angel, who took it with a blush. “Okay, Cas, your turn to judge. What’s the card?”

Cas reached over and picked up a black card. “And the academy award for…goes to…”

“Okay, this is a two-card one,” Jess said. “Cas, close your eyes. Everyone else, the card for the first blank goes on the bottom, the card for the second blank goes on the top.”

Charlie immediately slapped down two cards with a very self-satisfied grin. Jess gave her a quick glance and also put down two cards. Jo sighed, picking out two cards and placing them down, while Dean took his merry time rifling through his hand, picking two, re-thinking it and putting one back in favor of another one, changing the order, and altogether discarding the two cards he had picked. Finally, he put two down and Cas opened his eyes.

Cas picked up one stack of cards. “And the academy award for an asymmetric boob job goes to Miley Cyrus at fifty-five.” He frowned. “I don’t understand that reference,” he said, and plowed right on. “And the academy award for not giving a shit about the third world goes to God. Well, to be fair, God also did not give a shit about any other part in the world for a good while.” He picked up the third stack. “And the academy award for half-assed foreplay goes to a middle-aged man on roller skates.” He made a face. “I am not exactly sure what foreplay is, but I assume it is something related to sex, and I personally would not want to have sex with a middle-aged man on roller skates.”

“Foreplay happens before sex,” Charlie said quickly. “Just so you know for the future.”

“Oh,” Cas said, picking up the fourth stack. “And the academy award for a lifetime of sadness goes to Justin Bieber. I don’t understand that reference either. I think the one about God and the third world makes the most sense,” he said with a nod. “I will therefore pick that one.”

Charlie whooped. “That one was mine! Yes!” She took the black card happily.

“I think the middle-aged man one was pretty good,” Dean said, miffed. “I was trying to go literal, you know? Since I figured Cas wouldn’t get the other references.”

“My apologies, Dean. If I had known what foreplay was –”

“I was kidding,” Dean interrupted. “It’s fine. It’s a game.” He turned to Charlie. “Your turn to judge now. Pick a card.”

Charlie did.

The game went on for quite a few rounds, during which Charlie amassed quite a stack of black cards; she was proudest of winning the card “my life is ruled by a vicious cycle of…and…” with the cards “demonic possession” and “daddy issues” while Dean, who was not far behind her in terms of the number of black cards he had won, was judging. “Obviously, the gays have the ability to teleport over long distances” was another one she was particularly proud of; Dean and Cas had no idea why she and the other girls were snickering over her choice of card.

Dean had just won a round, bringing him to a tie with Charlie, and was judging now. “Alright guys, here’s the card: lovin’ you is easy ‘cause you’re…” He trailed off expectantly. “Give it your best shot.”

Cas immediately set a card down, looking very pleased with himself. Charlie rifled through the cards in her hand, snorted as she came across the second-to-last one, and promptly slapped it down. Jess picked a card and cocked her head to one side, pursed her lips, picked another card, pursed her lips again, and then put the first card down.

Jo, on the other hand, made a face. “Really? I don’t have _any_ good cards for this…” She sighed and put down a card. “That’s all I have, sorry. Now look away as I shuffle them, Dean, I know you saw which cards each of us put down.”

Dean closed his eyes obediently, opening them when Jo finished and Charlie poked him on the shoulder to let him know.

The four cards now all sat in front of Dean, face up. He ran a careful eye over all of them, muttering the answers to himself. “Lovin’ you is easy ‘cause you’re Harry Potter erotica, that’s terrible…wait, ‘Barack Obama?’ Jesus, that’s just plain weird, man. ‘Me.’ Well, I mean, I guess that could work, yeah. Oh, ha, lovin’ you is easy ‘cause you’re my genitals, that has gotta be the best one. Certainly the most relatable.” He sat back with a smirk. “Alright, guys, who had my genitals?”

Charlie let out a whoop. “Me! Oh, me me me! Yes! I’m winning!” She added the black card to her growing pile triumphantly.

Cas frowned. “I don’t understand. Whenever Sam thanks Obama you always laugh, so I assumed that loving him would be easy for you.”

Dean chuckled. “It’s called a meme, Cas. Sam introduced them to me last week. You’re not supposed to take it literally.”

Cas kept frowning. “But…loving Barack Obama…”

Jess sighed. “And I thought ‘Harry Potter erotica’ stood a chance.”

“That card doesn’t even make sense,” Dean pointed out with a grin. “Lovin’ you is easy ‘cause you’re Harry Potter erotica? Come on. Let’s be a little more mature than that.”

“Mine was definitely better,” Cas insisted. “‘Harry Potter erotica’ does not make sense.”

Jo shook her head, smiling. “It’s not _that_ bad of a card, guys.”

Charlie nodded enthusiastically. “Not as good as mine, but still not bad!”

“It’s a _terrible_ card,” Dean retorted. “ _I’m_ the judge, so anyone who disagrees with me can go suck a dick.”

Charlie and Jo raised their eyebrows.

“ _Really_ , Dean? That’s the best you can do?” Jo teased.

“‘Let’s be a little more mature,’” Charlie quoted, snickering, “so you automatically go to blowjobs. Uh huh. Very mature.”

“I agree with Charlie and Jo,” Cas announced abruptly.

“Hey, I don’t need your snark too,” Dean said, affronted.

“No, I agree that ‘Harry Potter erotica’ is a good card.”

Dean blinked. “Wait, what? Cas, that’s not even your card.”

Cas met his gaze evenly. “I know.”

“Cas, what? Just a second ago you were wholeheartedly agreeing with me and now you’ve changed your mind?”

Cas squinted at Dean. “You just said that anyone who disagreed with you could go suck a dick,” he said, his voice completely even. “Therefore it should be obvious that sucking a dick is what I’m trying to do right now.”

Charlie, with great difficulty, managed to stifle her astonished laughter. Jo and Jess were not so fortunate.

Dean raised an eyebrow. Charlie was greatly impressed but a great deal more disappointed with his otherwise lack of reaction.

“I’m sure you can find time to go to a bar or something after this,” Dean replied evenly, and Charlie very nearly missed the hurt in his voice.

Cas frowned. “What does a bar have to do with anything?”

Dean’s other eyebrow migrated up his forehead to join the first. “A bar? You know, the place where there’s a bunch of alcohol? Weird lights? Hot dudes? Ones you can take home with you?”

Cas squinted harder at him. “Why would we have to go to a bar then, if we are just to come directly back here?”

Dean spluttered. “‘We?’ No, Cas, I wouldn’t be going with you.”

“I don’t understand. Then what is the point of me going to a bar?”

Dean looked increasingly pained. “Cas, you…you go to a bar to find someone else to take home with you, where you can do whatever the hell you want I don’t need to know the details. You said you wanted to…do whatever, so you go to a bar, find some hot dude who strikes your fancy, and you take him home with you to do it.”

Cas was still confused. “Dean, I want to suck a dick right now, not wait until after this game is over and go to a bar.”

“You don’t _have_ to wait until the game is over, Cas, you can go right now if you want. There’s no one stopping you.”

Dean was getting frustrated. This was definitely _not_ the way things were supposed to go.

“I still don’t see the point in going to a bar.”

“Oh, for God’s sake, Cas!” Dean threw down his hand of cards. “I don’t know what you want me to say. The only dick in the room right now is mine, and –”

“Yes, exactly.”

Dean froze. So did Charlie and Jess and Jo.

Dean’s voice rasped in his throat when he spoke a few minutes later. “Cas…Cas, what?”

“I want to suck a dick right now, and the only dick available at the moment is yours. So, if you would be willing –”

“No! Wait, no, not no, Cas, I mean yes…I mean, I…”

“Okay, so we’ll be going now,” Charlie announced loudly, putting down her cards and getting to her feet. Jess was already standing and edging towards the door. “We’ll exit the room now and leave you to your talk, see you guys later!” She pulled a wide-eyed Jo to her feet and scrambled out of the room as fast as she could, practically slamming the door behind her.

This was a once-in-a-lifetime opportunity for the two thickheaded hunters, and she wasn’t about to let herself or anyone else ruin the moment.

She would be listening to the whole thing through the door, of course.

 

 

 

 

 


	7. Chapter 7

**Summary for the Chapter:**

> There's really no escaping what just happened, so they are forced to confront Cas's rather explicitly stated desire to suck Dean's dick. In other words, it's the obligatory awkward sex chapter.

 

 

“Cas,” Dean said hesitantly. “What…what was that about?” He looked edgy, like he was getting ready to flee. Dean was a fighter, but not when it came to emotions. In fact, one might have aptly described him as a deer caught in the headlights of a car. Or an impala.

Cas met his gaze. “I want to have sex with you.”

Dean swallowed hard, and Cas’s eyes followed the bobbing of his throat. “Um. Well. Well, that was…unexpected. I really…I didn’t…” He broke off and started again. “But _why_?”

Cas looked down, flustered for the first time. “I…that’s not what I really meant. Well, I mean, yes, that _is_ what I meant, but there’s more, it’s not just…” He trailed off. “I was advised to be direct about my feelings, and that…that was as direct as I could get.”

“You were _advised_? Cas, what?”

“I…yes. Sam. He told me to be more direct about my feelings.” Cas shuffled his feet. “But what I really mean is…I…I really like you. A lot. I think I might…love you. So I…I…” He trailed off awkwardly.

Dean’s mouth was hanging open. “You…you love me?” he whispered.

Cas’s cheeks reddened. “I understand if it’s not mutual,” he said quickly. “I mean, why would someone like you love someone like me? You are wonderful, and strong, and brave, and you have saved the world multiple times and are very popular with women, whereas I’m just an angel who doesn’t quite understand a lot of the references you make or how phones work or things like personal space, so if you don’t feel the same for me, I –”

“Cas,” Dean interrupted. “Shut up.”

Cas closed his mouth, biting his lip, looking utterly wretched. “Sorry,” he mumbled. “Sorry, I knew I shouldn’t have brought it up, I knew it would only make things weird since you obviously –”

“No,” Dean said quickly, stepping forward and taking Cas’s hand for a moment before he dropped it again in embarrassment. “No, Cas, that’s not…” He broke off and took a deep breath, uncharacteristically flustered. “It was nonsense,” he said finally, looking up at Cas. “What you were saying was nonsense, that’s why I told you to shut up. I mean, why would I _not_ love someone like you?” He broke off again, blinking. “I mean – well, yes, I…” He blushed.

Cas blinked. “You…you…”

“I love you too, dumbass,” Dean said with a laugh, still blushing and looking slightly astonished as if he didn’t think he would ever say something like that, so bluntly, to Cas. He took a step forward, closing the distance between them, biting his lower lip in a way that made Cas dizzy and almost faint. Hesitantly, he brought a hand up to Cas’s face, and Cas didn’t pull away. His ears flushed red. “You said you wanted to suck my dick, but can I…can I kiss you first?” he asked softly.

Cas inhaled a little too quickly, and he felt a little dizzier. “Oh,” he said. “I…yes. Yes. Certainly.”

Dean grinned, and leaned forward and pressed his lips to Cas’s.

Cas sighed and melted against him, finding to his confusion that his hands somehow moved on their own and were now clasped together behind Dean’s neck. There was also the feeling that something hot was pooling deep inside of him and something was happening between his legs that had only happened a few times before that he still didn’t understand, but then Dean’s tongue nudged his lips open and licked into his mouth and he was grinding against him and it felt so _good_ , and he decided not to question it.

He felt Dean’s hands on his body, first on his shoulders, then moving down to his sides, teasing lower but still unsure how far he could go, but Cas wanted _more_. He let out a frustrated noise, gripping Dean’s hand and placing it firmly on his ass.

Dean huffed a laugh, giving his ass a squeeze and kissing him harder, and the things that were happening in Cas’s body were making him hard.

“Do I do what the pizza man did?” he asked softly against Dean’s lips. He pictured himself between Dean’s legs, claiming him, taking him, and felt himself grow dizzy at just the thought.

“The – oh.” He sensed Dean’s surprise, and then felt his nervous grin. “Yes. Do that.”

Dean put his arms around Cas’s neck and Cas picked him up effortlessly. Dean wrapped his legs around Cas’s waist, kissing him harder now, mouthing his neck and jaw and sucking bruises as Cas carried him towards the door, only walking towards his destination because Dean absolutely hated it when Cas zapped him anywhere; there were only three words in Cas’s mind.

_Dean. Bed. Now._

They made it to the bed, completely missing the Shipping Girls standing just outside and their identical shocked faces as they walked past them. Or, rather, as Cas walked past them, carrying Dean. Cas wasn’t quite sure whose bed it was that he and Dean ended up on, since he had headed towards the first room he had seen with a bed in it and in his flustered and Dean-filled craze he couldn’t quite remember whose room it was, but Dean didn’t seem to care, so Cas just went with it.

“Cas,” Dean gasped, as Cas lay him down on his back and proceeded to kiss every inch of skin that he could find.

It wasn’t enough. Not nearly enough skin. He practically ripped Dean’s shirt off of him, and suddenly there was much more skin that he could ravage. He leaned down and kissed down Dean’s chest, shedding his own clothes in the process, sucking bruises into Dean’s skin and touching him anywhere, everywhere. Dean kicked off his pants underneath him and then he felt Dean’s hands on his hips, bringing him closer, and then there was the most wonderful feeling of friction against his erect dick. He gasped and shuddered, freezing with the sudden sensation.

“Cas?” Dean asked softly. “Cas, are you okay?”

Cas blinked rapidly. “Yes. Yes, more than okay.” He tentatively reached a hand down between them, his hips jerking forwards as he grasped his length in his hands.

“Have you…have you done this before?” Dean asked, a hint of amusement in his voice.

Cas shook his head. “No. I…I am mostly going on…instinct.”

Dean chuckled. “You’re doing pretty well, then.”

“I…I want to suck your dick,” Cas proclaimed.

Dean’s breath hitched. “O-okay. Um. Yes, yes that’s –”

Cas leaned down and took Dean’s length in his mouth. Dean gasped, his hips bucking up off of the bed, involuntarily thrusting into Cas’s throat, causing him to gag, before he bit his lip and forced himself to stay still.

Cas pulled off almost completely and swirled his tongue experimentally around the tip of Dean’s penis, grinning when it caused him to cry out, fisting at the sheets. He swirled his tongue again and then plunged his head down, enveloping Dean’s length in the heat of his mouth, his throat working.

“Oh God, Cas, don’t stop –”

He didn’t. He bobbed his head up and down and felt Dean’s hands come to tangle in his hair, holding him steady as he sucked, doing his best to suppress his gag reflex. Dean moaned, his legs spreading, his face flushed with arousal. He writhed, his breaths coming faster and harsher as Cas pushed him towards the edge.

Cas released him with a wet pop, looking up at him with an uncertain smile as Dean whined at the sudden lack of contact. “Dean, was that…was that satisfactory?”

“Satisfactory? Jesus Christ, Cas, that was _way_ more than satisfactory,” Dean gasped. He bit his lip, looking suddenly anxious and embarrassed but still a whole lot aroused. “I want…I want you to fuck me.”

“You mean like the pizza man?” Cas asked.

Dean huffed a laugh, his voice tight. “Uh, yes, like the pizza man. You’ll need –” He broke off as a bottle of lube appeared in Cas’s hand, and shook his head in surprise and amusement. “There’s a bottle in the nightstand, you didn’t have to summon one with your angel magic.”

“It was faster,” Cas said, already squirting some of the cold lube into his palm and rubbing it onto his cock, shuddering as his touch sent pleasure shooting through his body. “If…if I remember correctly, there was preparation involved first,” he said. “With the fingers.”

Dean looked impressed and also a great deal aroused at Cas’s bluntness. “Damn, that was some quality porn you were watching.” He grinned nervously. “Yeah, it was right.”

Cas bit his lip, touching Dean’s thigh gently. Dean spread his legs apart, exposing himself, his face flushed. He let out a gasp as Cas’s finger brushed against his hole; Cas caught it with a kiss, pushing a finger into him while he rubbed at Dean’s chest with his other hand. Dean whined, his hands on Cas’s sides, stroking and touching.

“Is this correct?” Cas asked, a quite comical look of concern on his flushed face.

“Yes – yes, it’s good,” Dean gasped out. “More than good. Keep going.”

Cas rubbed a second finger around Dean’s entrance before pushing it in gently; Dean let out a soft cry and Cas stopped, looking very nearly panicked.

“Are you alright? I didn’t hurt you, did I? I can stop if you would like, I apologize if I did anything wrong –”

“No,” Dean gasped, interrupting him. “No, you’re good, just…give me a sec.” He took a deep breath. “Alright,” he said. He blushed. “I just…I’ve never done this with anyone else before.” He gasped again as Cas began scissoring his fingers, stretching him out, preparing him. He let out a cry as Cas’s fingers brushed past his prostate, his hips bucking and his legs spreading wider.

“Oh Gods, _fuck_ , Cas, yes –” he choked out.

Cas blushed heavily. “Dean, I…as much as I find your expletives extremely arousing, I must ask you to stop using my father as one of them,” he mumbled.

Dean huffed a laugh, his voice still tight as Cas continued to stretch him out. “Okay. Sorry, I’ll do my best to find another – oh, _fuck_!” he yelled as Cas added a third finger; Dean whined, arching off of the bed and his fists clenching, tearing at the sheets, Cas’s fingers rubbing deliciously against his prostate. His hands reached down towards his erect length, stroking it and moaning, shudders of pleasure running through his body.

Cas continued scissoring his fingers, twisting and stretching, wanting to make sure Dean was prepared enough so that it wouldn’t be painful when he took him. “Is this sufficient?” Cas asked, sounding much more breathless than usual.

“Yes,” Dean gasped. “Kiss me, Cas, please –” He broke off, whining at the sudden emptiness as Cas withdrew his fingers.

Cas leaned down and kissed Dean fiercely, lining the tip of his dick up with Dean’s hole and pushing in gently. Dean gasped again, his hips bucking, but shook his head and whined in frustration when Cas stopped, so Cas kept pushing in slowly until he was completely sheathed in Dean’s heat.

Dean was shaking slightly, his eyes wide with the feeling of being filled. Cas watched him in concern, staying still while Dean grew accustomed to the feeling. Then something inside him seemed to give way and a shudder ran through his body; taking this as a sign that he was ready, Cas drew out almost completely and then pushed back in, a shocked huff of breath escaping him as the pleasure of the friction and heat rushed through him.

“Holy fucking hell,” Dean gasped, and his hands reached down to grip Cas’s hips, holding him steady as he thrust into him again and again.

“Dean,” Cas choked out, his own hands on Dean’s sides, squeezing tight enough to leave bruises; he kissed him again, mouthing along his jaw and the side of his neck, kissing his collarbones and his chest as he kept thrusting into Dean’s heat.

Dean clenched down around him as Cas said his name, his mouth open with a hoarse cry. He moved a hand in between their bodies to his cock, but Cas batted it away, taking it in his own hand instead and stroking in time with his thrusts. He was only vaguely aware of and certainly didn’t care at all about the banging of the bed against the wall.

“Jesus – I mean, holy shit,” Dean gasped, his pupils blown, his lips swollen and kiss-red, his cheeks flushed and heated, his chest heaving with harsh breaths. He clenched down around Cas again and Cas let out a soft cry as the heat enveloped him, overwhelmed him, pushed him towards the edge.

He felt the heat coiling in his belly, felt the throbbing in his hardness, and when he looked at Dean, vulnerable and submissive and writhing in pleasure beneath him, he knew he wasn’t going to last long.

He leaned down and kissed Dean again, using his teeth this time to nip at the sensitive skin of his neck, his earlobe, his lower lip, pleasure flooding his veins as Dean whined in response.

“Cas, I can’t – I’m going to come –” Dean choked out, and Cas’s pace quickened. A moment later, he came in Cas’s hand with a harsh cry of his name, his seed spilling hot and sticky into his fingers and some of it splattering against his belly.

Cas felt the heat building, knew he was going to go over the edge any second, and his hand tightened on Dean’s side. “Close your eyes,” he managed, and Dean obeyed just in time to avoid having his eyes being burned out as Cas’s grace flashed white-hot, bursting through the room, shattering lightbulbs, casting the shadow of his flared wings onto the ceiling. Dean’s name tore from his lips in a scream and his body shuddered as he came into Dean, taking him with his seed.

The light of his grace faded as he collapsed onto Dean, panting, utterly spent.

“Holy shit, Cas,” Dean whispered, tired and awed at the same time.

Cas ducked his head, blushing. “I…I apologize, Dean. I will replace the lightbulbs, seeing as it was my fault that they have…exploded.”

Dean huffed a laugh, wrapping his warm arms around him and kissing the top of his head. He laughed again, kind of stunned, kind of exhilarated, as if he couldn’t believe what had just happened. “It’s okay, Cas, don’t worry about it.” He swallowed. “That was…that was awesome, Cas.”

“I didn’t think we would ever do it,” Cas mumbled into his chest. Their bodies were sticky with seed, and he waved it away with a hand.

“Are you…are you happy that we did?” Dean asked cautiously.

“Yes,” Cas whispered. “Are you?”

Dean laughed again, pushing Cas off of him and rolling over so he was on top of him. He kissed him gently, and his green eyes were sparkling with laughter. “Yeah.” He huffed and flopped down on the bed next to Cas, hesitantly reaching up a hand and touching his cheek. Cas’s eyes flickered up to meet his gaze and he blushed, lowering his hand from his face.

“It’s alright,” Cas murmured, so Dean brought his hand up again, touching the contours of his face before moving down to his shoulders, his chest.

“I love you,” he said quietly.

Cas flushed with pleasure. “I love you,” he echoed.

Dean grinned, snuggling closer to Cas, his eyelids already drooping with post-sex exhaustion. Cas put his arms around him and pulled the covers over them, and they both fell into sleep.

 

 

Cas woke a few hours later. Dean was already awake and out of bed, pulling on his jeans. He fastened the belt and picked up his shirt from the floor with exaggerated caution, clearly thinking that Cas was still asleep. He wiggled into it and headed towards the door.

“Where are you going?” Cas mumbled sleepily.

Dean looked back at him. “You said you were advised to be more direct about your feelings?”

Cas squinted, which, because his eyes were already only half-open, caused them to be almost closed, and frowned. “Um. Yes. Is that a bad thing?”

“No. I appreciate it, seeing as it ended up with you fucking me into the wall until it cracked – I’m going to have to fix that later. But uh, Sam meddling in my relationships makes me a bit…well, it’s a bit weird, isn’t it? So yeah. I’m going to have a few words with Sam.”

Cas gave a soft chuckle. “Okay. Maybe talk to the girls, too. They were the masterminds of it.”

Dean lifted an eyebrow. “Goddamn it,” he muttered. “They’re going to give me hell. Probably call me emotionally constipated or something like that.” Shaking his head, he left.

As soon as he had left the room, Gabriel appeared at the foot of the bed. He let out a very un-angelic shriek at Cas’s nakedness and covered his eyes, making an exaggeratedly traumatized face. “For fuck’s sake, Cas, put some clothes on!”

Cas rolled his eyes and waved his hand, his familiar clothes appearing back on his body. “What?”

Gabriel peeked out from between his fingers, and when he saw that Cas was appropriately clothed, he lowered his hand and smirked. “Two things, bro. For one, watch the noise. Jesus _fuck_ , that was loud. I think you guys are louder than me and Sam, and that’s saying something. Doesn’t help that I can hear _everything_ that’s going on through our angel-fi. For two, maybe tone it down a little bit in terms of the fucking? You’re about to break the wall, you know. I heard some cracking in the foundation.” He glanced around the room, his eyebrows raised. “And…just as I thought,” he sighed. “I take it back; there are three things. The third: you really gotta watch it with your grace. You blew out the electricity.”

Cas flushed and crossed his arms. “My apologies,” he muttered.

Gabriel grinned at him. “On that note, though, congrats. You finally got your man.”

Cas couldn’t hide a smile.

Yes. He did.

 

 

Two rooms down the hall, in the face of Dean’s rather embarrassed glower, three girls (and Sam) cheered in triumph.

 

 

 

 

 


End file.
